Three months ago I would have told you I’d never take seriously enough to write about Amazon’s house-brand shoes. Today, I’m telling you that I own a pair of $50 loafers from Amazon that nobody can identify as non-Robergiano. I’ve even received compliments on them.

Margaret thinks this means I’ve hit rock bottom. Let’s hope she’s wrong. Background: The Aldens were purchased in what I will generously refer to as “difficult financial times,” which means they are now four years old and beyond repair.

My longstanding dilemma – expensive hobby paying substantially lower-than-lawyer salary – is as old as ever, and I was facing a week of depositions and meetings where I would actually have to dress like an adult human being. I decided to buck tradition and order a pair of the Amazon loafers that my coworker David’s nephew (college finance dude living in NYC) had purchased and which were apparently fooling everyone.

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David knows nothing about real shoes; he is literally the dude who once asked me if cordovan comes from an exotic species of pigeon.

But desperation is desperation, and when faced with showing up to a week of important meetings wearing shoes that resemble sagging cement boils wrapped around your feet, you cast aside preconceived notions and open Amazon.com. I clicked through dozens of sobering browser tabs before collapsing into bed empty-eyed at 3am. I repeated this process twice more before finally accepting that I would be wearing my rotting sandals for the week.

When David mentioned the Amazon loafers later that morning, I decided to bite. Friend of ManagementConsulted, send me that link. The loafers arrived two days later.

I opened the Amazon box like a drug lord inspecting a new shipment, half-expecting molded plastic hoof-shaped objects the size of my feet to jump out and attack me. Instead…I pulled out these. That’s real leather on those shoes, folks – not the “faux leather materials made from plastic” rubbish you typically get from Amazon.

The colour is on the lighter side, but not unpleasant. The hardware feels like it has some heft to it and is properly scaled. You can obviously see the rubber sole, but hey: clean edges, no visible glue lines.

Are they great shoes? No. Are they in the same league as my best footwear?

Absolutely not. The leather doesn’t have that supple, fatty feel that high-end Italian calf provides, the stitching isn’t hand-done (duh), and they just lack the overall streamlined shape of something constructed by artisans with no concept of an hourly wage. Do they pass for way more expensive than they are in combination with appropriate trousers?

Absolutely! I decided to put them to the test that evening at a small firm dinner: no skin off my back if they autumn apart and people make fun of me. Fellow counsel started giving me compliments within thirty minutes of arriving.

One of the partners from opposing counsel thought they were vintage Gucci loafers due to the slightly deeper patina from wear as opposed to this season’s shade of tan. “That’s not a vintage Gucci loafer you have on,” he said with a laugh. I shrugged and changed the subject because it’s never fun to admit you duped people into thinking your shoes are worth five times what you actually paid for them. Plus I felt guilty about besting my gentleman adversary in the Old Money Olympics.

The guilt didn’t last long, however, because Robert admitted earlier that day he spent thirty minutes going on and on about how “nice” his Jordans were. Thirty minutes. He spent THIRTY MINUTES telling me how awesome his Jordan trainers were.

They were probably fake Jordans. Anyway: I began work on my senior thesis. Over the next month I tested these loafers out in all sorts of combinations to see where the lines were drawn.

You’d be shocked – horribly shocked – at how often people assume your shoes are way nicer when paired with properly tailored trousers and a quality dress shirt. Traditionalists, raise your hand if you hate me right now. The Results: Properly dressed (including suitably tailored trousers, a button-up shirt, and one of my nicer blazers), I cannot wear these shoes in any capacity without someone commenting on them and assuming they cost significantly more than $50.

On at least three separate occasions someone asked if they were “new Gucci” because they liked the deeper tone relative to what Gucci was currently offering. Casual jeans and a tee shirt? Mid-range shoe that doesn’t scream dollar-store purchase.

Nobody would confuse these for something expensive, but they also don’t scream Walmart No Name Brand, either. The consensus from observers appears to be Cole Haan or some other faux luxury brand you might pick up at the mall. Perfectly acceptable shoes for casual Friday or weekend client dinners, but nothing that would ever pass as an intentional professional timepiece.

The only person who correctly identified them was Tom Richardson (mentioned above), my fellow elder statesman of traditional menswear snobbery. We were getting drinks after a bar association event when he caught me staring down at my feet and chuckled. “Amazon ones, right?” Tom asked. “Not too bad for the price, huh?” I wanted to hug him. Instead I poured him a drink and had him swear to eternal secrecy should he ever discover my well-hidden Internet-blog-hiding-spot.

How do $50 shoes manage to pass for $500+ ones? Details, my friends. Details.

Tip #1: Condition that leather ASAP. As soon as you take those puppies out of the box, they need to be conditioned. I used Saphir Renovateur because I have issues, but use whatever leather conditioner you prefer.

It’ll darken the leather up just a touch and give it a nice luster that makes them appear infinitely more expensive than they are. Trust me. Tip #2: Your trousers make or break your shoes.

When wearing cheap shoes, they look cheapest when you’re wearing poorly fitting trousers. Make sure you have just a slight break where your trousers kiss your loafers. Too much fabric pooling around your ankles looks like you tried too hard.

Trousers ends that float too far above your shoes make you look like you’re preparing for Noah to come. Tip #3 – Invest in some decent socks. White tube socks with your dress shoes screams amateur faster than anything else.

Dress socks are your friend here. Get thick over-the-calf dress socks that coordinate with your trousers so that when you sit down and your pant leg naturally rides up you’re showing off style choices as opposed to accidentally flashing your yoga gear. Tip #4 – Maintain them.

Once cheap shoes start to look scuffed and worn out, people will notice. They instantly become cheap shoes. I keep leather maintenance supplies at my office now so I can spritz and shine these babies up before any big meetings.

Two minutes of love and attention pre-meeting can make all the difference. Tip #5: Act like they’re expensive. If you can smuggle your baby Guccis into the office in an ikea bag but act like you just dropped a grand on them, you’ve got life figured out.

Just wear these shoes with confidence and you’ll fool every Tom, Dick, and…Howard. Hey, guys. TLDR: Buy some loafers from Amazon.

You’ll thank me. Is this an endorsement to throw out your beloved shoes and swap them all out for Amazon alternatives? Of course not.

I love my Aldens. I love my birthday Church’s. I love my Edward Greens that I found at an estate sale and may or may not be the best shoes I own.

None of those are going anywhere, and quite frankly you’re cheating yourself if you don’t own at least one pair of truly amazing shoes that you’ve broken in and will wear until your go schlepping grapes in Argentina. But life is weird right now. Inflation sucks and costs too much for everything, Margaret and I just found out our property taxes are going up AGAIN (the FUCK?) and sometimes you need something to wear around town that doesn’t break the bank or require a trip to Christie’s.

Your Amazon loafers fit the bill nicely. Earlier this year I took a week-long trip to Chicago for a conference. Running late to my first meeting after pouring an entire pot of coffee on myself in the hotel room bathroom (white shirts before coffee are my new thing, obviously), I grabbed the loafers and dashed for the conference centre.

Literally walked around Chicago for four days giving depositions and meeting with opposing counsel, expert witnesses, and clients who are pretty damn well versed in these types of details. Not one single person questioned my footwear. In fact, I received several compliments, including one from the expert witness himself – a dude who I’m pretty sure could tell nice shoes when he sees them based on his Hermès leather belt and what was unmistakably a Turnbull & Asser shirt who paused mid-conversation to ask where I procured my “interesting” alternatives to traditional loafers.

I’m sure they were expensive Italians, but hey – they were wondering about mine!

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I wanted to blurt out the truth. Where I found them.

That they were less than 10% of the price of his shoes. Professional pride: 1, Truth: 0. It felt good to win.

Hopefully I never find out who lost. So here’s what I love about the whole experience: us Old Money hipsters bragging about how we’ve got actual skilled artisans making our shoes back when Italy was still a province of Fascist Germany have been missing the point all along. Just because something costs more doesn’t mean it’s automatically better.

Just because something is available to the plebs at an affordable price point doesn’t mean you can’t look awesome wearing it. Hell, now I own TWO pairs of $50 loafers from Amazon that nobody can identify as coming from anywhere but Italy. Progress!

Author carl

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